(7S,9S)-9-[(1-13C)acetyl]-9-amino-7-{[(2S,4R,5R)-4,5-dihydroxyoxan-2-yl]oxy}-6,11-dihydroxy-5,7,8,9,10,12-hexahydro(4a,12a-13C2)tetracene-5,12-dione

• ChemBase ID: 160598
• Molecular Formular: C25H25NO9
• Molecular Mass: 486.44526451
• Monoisotopic Mass: 486.1629959
• SMILES: c1ccc[13c]2[13c]1C(=O)c1c(C2=O)c(c2c(c1O)C[C@](C[C@@H]2O[C@@H]1OC[C@@H](O)[C@H](C1)O)([13C](=O)C)N)O
• Canonical SMILES: O[C@@H]1CO[C@H](C[C@@H]1O)O[C@H]1C[C@@](N)(Cc2c1c(O)c1c(c2O)C(=O)[13c]2[13c](C1=O)cccc2)[13C](=O)C
• InChI: InChI=1S/C25H25NO9/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3/t14-,15-,16+,17+,25+/m1/s1/i10+1,11+1,12+1
• InChIKey: VJZITPJGSQKZMX-VCKZGHBQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7S,9S)-9-[(1-^1^3C)acetyl]-9-amino-7-{[(2S,4R,5R)-4,5-dihydroxyoxan-2-yl]oxy}-6,11-dihydroxy-5,7,8,9,10,12-hexahydro(4a,12a-^1^3C₂)tetracene-5,12-dione
• IUPAC Traditional name: (7S,9S)-9-[(1-^1^3C)acetyl]-9-amino-7-{[(2S,4R,5R)-4,5-dihydroxyoxan-2-yl]oxy}-6,11-dihydroxy-8,10-dihydro(4a,12a-^1^3C₂)-7H-tetracene-5,12-dione
• Synonyms: (7S,9S)-9-Acetyl-9-amino-7-[(2-deoxy-β-D-erythro-pentopyranosyl)oxy]-7,8,9,10-tetrahydro-6,11-dihydroxy-5,12-naphthacenedione-13C3; Amrubicin-13C3

Database IDs

• PubChem SID: 162254733
• PubChem CID: 71313392

CALCULATED PROPERTIES

• Acid pKa: 9.2586775
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 0.5010348
• LogD (pH = 7.4): 1.8919419
• Log P: 2.0625176
• Molar Refractivity: 122.0095 cm^3
• Polarizability: 47.644547 Å^3
• Polar Surface Area: 176.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Orange Solid
• Melting Point: >240°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A635202

Synthetic anthracycline antibiotic; inhibits DNA topoisomerase II. Antineoplastic.

REFERENCES

• Igarashi, J., et al.: Bioorg. Med. Chem Lett., 5, 2923 (1995)
• Hanada, M., et al.: Jpn. J. Cancer Res., 89, 1229 (1995)
• Ohe, Y., et al.: Ann. Oncol., 16, 430 (1995)
• Matsunaga, Y., et al.: Ther. Drug Monit., 28, 76 (1995)